Synonym
RK 397; RK-397; RK397;
IUPAC/Chemical Name
(3Z,5Z,7Z,9Z,11Z,29Z)-32-ethyl-14,16,18,20,22,24,26,28-octahydroxy-15,31-dimethyloxacyclodotriaconta-3,5,7,9,11,29-hexaen-2-one
InChi Key
WXZBVOYYWCPWLJ-QBRXNAHSSA-N
InChi Code
InChI=1S/C35H56O10/c1-4-34-24(2)16-17-26(36)18-27(37)19-28(38)20-29(39)21-30(40)22-31(41)23-33(43)25(3)32(42)14-12-10-8-6-5-7-9-11-13-15-35(44)45-34/h5-13,15-17,24-34,36-43H,4,14,18-23H2,1-3H3/b7-5-,8-6-,11-9-,12-10-,15-13-,17-16-
SMILES Code
CCC1C(C)/C=C\C(O)CC(O)CC(O)CC(O)CC(O)CC(O)CC(O)C(C)C(O)C/C=C\C=C/C=C\C=C/C=C\C(O1)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
636.82
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Burova SA, McDonald FE. Total synthesis of the polyene-polyol macrolide RK-397, featuring cross-couplings of alkynylepoxide modules. J Am Chem Soc. 2004 Mar 3;126(8):2495-500. PubMed PMID: 14982459.
2: Kobinata K, Koshino H, Kudo T, Isono K, Osada H. RK-397, a new oxo pentaene antibiotic. J Antibiot (Tokyo). 1993 Oct;46(10):1616-8. PubMed PMID: 8244892.
3: Denmark SE, Fujimori S. Total synthesis of RK-397. J Am Chem Soc. 2005 Jun 29;127(25):8971-3. PubMed PMID: 15969572.
4: Guo H, Mortensen MS, O'Doherty GA. Formal total synthesis of RK-397 via an asymmetric hydration and iterative allylation strategy. Org Lett. 2008 Jul 17;10(14):3149-52. doi: 10.1021/ol801055b. Epub 2008 Jun 13. PubMed PMID: 18549226.
5: Mitton-Fry MJ, Cullen AJ, Sammakia T. The total synthesis of the oxopolyene macrolide RK-397. Angew Chem Int Ed Engl. 2007;46(7):1066-70. PubMed PMID: 17051569.
6: Koshino H, Kobinata K, Isono K, Osada H. Structure of RK-397, a new oxo pentaene antibiotic. J Antibiot (Tokyo). 1993 Oct;46(10):1619-21. PubMed PMID: 8244893.
7: Das VN, Siddiqui NA, Verma RB, Topno RK, Singh D, Das S, Ranjan A, Pandey K, Kumar N, Das P. Asymptomatic infection of visceral leishmaniasis in hyperendemic areas of Vaishali district, Bihar, India: a challenge to kala-azar elimination programmes. Trans R Soc Trop Med Hyg. 2011 Nov;105(11):661-6. doi: 10.1016/j.trstmh.2011.08.005. Epub 2011 Sep 25. PubMed PMID: 21945327.
